diff --git a/src/client/datascience/interactive-ipynb/nativeEditor.ts b/src/client/datascience/interactive-ipynb/nativeEditor.ts
index 0ae442b19afb..7eeb259016fc 100644
--- a/src/client/datascience/interactive-ipynb/nativeEditor.ts
+++ b/src/client/datascience/interactive-ipynb/nativeEditor.ts
@@ -252,7 +252,7 @@ export class NativeEditor extends InteractiveBase implements INotebookEditor {
 
         // Sign up for dirty events
         model.changed(this.modelChanged.bind(this));
-        this.previouslyNotTrusted = model.isTrusted;
+        this.previouslyNotTrusted = !model.isTrusted;
     }
 
     // tslint:disable-next-line: no-any
diff --git a/src/client/datascience/interactive-ipynb/trustCommandHandler.ts b/src/client/datascience/interactive-ipynb/trustCommandHandler.ts
index 09ee31f49e62..cf866fd183f6 100644
--- a/src/client/datascience/interactive-ipynb/trustCommandHandler.ts
+++ b/src/client/datascience/interactive-ipynb/trustCommandHandler.ts
@@ -4,7 +4,7 @@
 'use strict';
 
 import { inject, injectable } from 'inversify';
-import { Uri } from 'vscode';
+import { commands, Uri } from 'vscode';
 import { IExtensionSingleActivationService } from '../../activation/types';
 import { IApplicationShell, ICommandManager } from '../../common/application/types';
 import { ContextKey } from '../../common/contextKey';
@@ -59,18 +59,25 @@ export class TrustCommandHandler implements IExtensionSingleActivationService {
             DataScience.doNotTrustNotebook(),
             DataScience.trustAllNotebooks()
         );
-        if (selection !== DataScience.trustNotebook() || model.isTrusted) {
-            return;
+
+        switch (selection) {
+            case DataScience.trustAllNotebooks():
+                commands.executeCommand('workbench.action.openSettings', 'python.dataScience.alwaysTrustNotebooks');
+                break;
+            case DataScience.trustNotebook():
+                // Update model trust
+                model.update({
+                    source: 'user',
+                    kind: 'updateTrust',
+                    oldDirty: model.isDirty,
+                    newDirty: model.isDirty,
+                    isNotebookTrusted: true
+                });
+                const contents = model.getContent();
+                await this.trustService.trustNotebook(model.file, contents);
+                break;
+            default:
+                break;
         }
-        // Update model trust
-        model.update({
-            source: 'user',
-            kind: 'updateTrust',
-            oldDirty: model.isDirty,
-            newDirty: model.isDirty,
-            isNotebookTrusted: true
-        });
-        const contents = model.getContent();
-        await this.trustService.trustNotebook(model.file, contents);
     }
 }